3-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-1-(2,6-dimethyl-4-nitrophenyl)pyridin-2(1H)-one → HCID 59410188, compound

HRID 85227Notes

Reaction equation

HRID 85227 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]1[C:22](=[O:38])[N:23]([C:27]2[C:32]([CH3:33])=[CH:31][C:30]([N+:34]([O-])=O)=[CH:29][C:28]=2[CH3:37])[CH:24]=[CH:25][CH:26]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[NH2:34][C:30]1[CH:31]=[C:32]([CH3:33])[C:27]([N:23]2[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:22]2=[O:38])=[C:28]([CH3:37])[CH:29]=1

Participants

3

Reactant 1

HCID 594101853-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-1-(2,6-dimethyl-4-nitrophenyl)pyridin-2(1H)-one

Product 1

HCID 59410188HCID 59410188, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

143 g (271 mmol) of the compound from Example 62A (alternative synthesis) are dissolved in 1.43 l of tetrahydrofuran and flushed with argon. 17 g of palladium on carbon (50%, moistened with water) are added, and the mixture is then hydrogenated at RT in a hydrogen atmosphere under atmospheric pressure. The mixture is then filtered through kieselguhr, the filter cake is washed with tetrahydrofuran and the filtrate is freed from the solvent. The reaction product (134 g) is reacted further without further purification.

Workup

  1. customflushed with argon
  2. addition17 g of palladium on carbon (50%, moistened with water) are added
  3. customis then hydrogenated at RT in a hydrogen atmosphere under atmospheric pressure
  4. filtrationThe mixture is then filtered through kieselguhr
  5. washthe filter cake is washed with tetrahydrofuran
  6. customThe reaction product (134 g) is reacted further without further purification

Sources & evidence

ORD record
ord-1df45794e0d5437ca3c665ee21f3d77d
Source dataset
uspto-grants-2014_09
Patent number
US08846934B2

Reaction notes

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